PL72695B1 - 1-substituted-4-aryl-2(1h)-quinazolinones and their preparation [us3723432a] - Google Patents

1-substituted-4-aryl-2(1h)-quinazolinones and their preparation [us3723432a] Download PDF

Info

Publication number: PL72695B1
Authority: PL; Poland
Prior art keywords: compounds; general formula; group; reacted; preparation
Prior art date: 1968-11-12

Application number

PL1969136872A

Other languages

English (en)

Polish (pl)

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1968-11-12

Filing date

1969-11-12

Publication date

1974-08-30

1969-11-12 Application filed filed Critical

1974-08-30 Publication of PL72695B1 publication Critical patent/PL72695B1/pl

Links

238000002360 preparation method Methods 0.000 title claims description 36
150000001875 compounds Chemical class 0.000 claims abstract description 130
238000000034 method Methods 0.000 claims abstract description 46
238000006243 chemical reaction Methods 0.000 claims abstract description 40
-1 methyl halide Chemical class 0.000 claims abstract description 21
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 9
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims description 47
239000002253 acid Substances 0.000 claims description 23
239000003960 organic solvent Substances 0.000 claims description 22
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 15
229910052801 chlorine Inorganic materials 0.000 claims description 14
229910052731 fluorine Inorganic materials 0.000 claims description 14
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
239000007868 Raney catalyst Substances 0.000 claims description 10
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 10
229910000564 Raney nickel Inorganic materials 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 10
239000011737 fluorine Substances 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 7
230000003197 catalytic effect Effects 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
238000005984 hydrogenation reaction Methods 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
239000002841 Lewis acid Substances 0.000 claims description 6
150000007517 lewis acids Chemical class 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
239000011230 binding agent Substances 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
150000001340 alkali metals Chemical group 0.000 claims description 4
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
239000011592 zinc chloride Substances 0.000 claims description 3
235000005074 zinc chloride Nutrition 0.000 claims description 3
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
150000004694 iodide salts Chemical class 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
239000004323 potassium nitrate Substances 0.000 claims description 2
235000010333 potassium nitrate Nutrition 0.000 claims description 2
239000012286 potassium permanganate Substances 0.000 claims description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Inorganic materials [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims description 2
239000004317 sodium nitrate Substances 0.000 claims description 2
235000010344 sodium nitrate Nutrition 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 6
238000004519 manufacturing process Methods 0.000 claims 4
FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 claims 3
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims 2
150000002466 imines Chemical class 0.000 claims 2
229910052740 iodine Chemical group 0.000 claims 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
DLGOLDCIEHQIMN-UHFFFAOYSA-N 2-(benzenecarboximidoyl)aniline Chemical compound NC1=CC=CC=C1C(=N)C1=CC=CC=C1 DLGOLDCIEHQIMN-UHFFFAOYSA-N 0.000 claims 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
ICPXMFSOUJYSHU-UHFFFAOYSA-N 6-(dimethylamino)-7-methyl-4-phenyl-1-propan-2-ylquinazolin-2-one Chemical compound C(C)(C)N1C(N=C(C2=CC(=C(C=C12)C)N(C)C)C1=CC=CC=C1)=O ICPXMFSOUJYSHU-UHFFFAOYSA-N 0.000 claims 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
230000007062 hydrolysis Effects 0.000 claims 1
238000006460 hydrolysis reaction Methods 0.000 claims 1
239000012442 inert solvent Substances 0.000 claims 1
238000005304 joining Methods 0.000 claims 1
150000007522 mineralic acids Chemical class 0.000 claims 1
150000007524 organic acids Chemical class 0.000 claims 1
150000003112 potassium compounds Chemical class 0.000 claims 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
229960000948 quinine Drugs 0.000 claims 1
150000001350 alkyl halides Chemical class 0.000 abstract description 2
238000007363 ring formation reaction Methods 0.000 abstract 2
JQSGYWDRDFLCPD-UHFFFAOYSA-N 1-ethyl-4-phenylquinazolin-2-one Chemical compound N=1C(=O)N(CC)C2=CC=CC=C2C=1C1=CC=CC=C1 JQSGYWDRDFLCPD-UHFFFAOYSA-N 0.000 abstract 1
229940035676 analgesics Drugs 0.000 abstract 1
239000000730 antalgic agent Substances 0.000 abstract 1
239000002260 anti-inflammatory agent Substances 0.000 abstract 1
229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
230000001754 anti-pyretic effect Effects 0.000 abstract 1
239000002221 antipyretic Substances 0.000 abstract 1
229940125716 antipyretic agent Drugs 0.000 abstract 1
239000000543 intermediate Substances 0.000 abstract 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
239000000243 solution Substances 0.000 description 5
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000002904 solvent Substances 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000008096 xylene Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical group 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
150000002431 hydrogen Chemical group 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 2
125000005270 trialkylamine group Chemical group 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
FHUBTSLLILWICW-UHFFFAOYSA-N 4-phenyl-1h-quinazolin-2-one Chemical class C12=CC=CC=C2NC(=O)N=C1C1=CC=CC=C1 FHUBTSLLILWICW-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 description 1
WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910001963 alkali metal nitrate Inorganic materials 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
125000000879 imine group Chemical group 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

PL1969136872A 1968-11-12 1969-11-12 1-substituted-4-aryl-2(1h)-quinazolinones and their preparation [us3723432a] PL72695B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US00775201A US3723432A (en)	1968-11-12	1968-11-12	1-substituted-4-aryl-2(1h)-quinazolinones and their preparation

Publications (1)

Publication Number	Publication Date
PL72695B1 true PL72695B1 (en)	1974-08-30

Family

ID=25103642

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL1969136872A PL72695B1 (en)	1968-11-12	1969-11-12	1-substituted-4-aryl-2(1h)-quinazolinones and their preparation [us3723432a]

Country Status (19)

Country	Link
US (2)	US3723432A (fr)
AT (4)	AT319950B (fr)
BE (1)	BE741529A (fr)
BG (10)	BG16042A3 (fr)
BR (1)	BR6914095D0 (fr)
CH (1)	CH521972A (fr)
DE (1)	DE1956384C3 (fr)
DK (1)	DK129347B (fr)
ES (1)	ES373377A1 (fr)
FR (1)	FR2024830B1 (fr)
GB (1)	GB1282612A (fr)
IE (1)	IE33933B1 (fr)
IL (1)	IL33348A (fr)
NL (1)	NL6916514A (fr)
NO (1)	NO124032B (fr)
OA (1)	OA03829A (fr)
PL (1)	PL72695B1 (fr)
SE (2)	SE374920B (fr)
ZA (1)	ZA697910B (fr)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3923803A (en) *	1968-07-18	1975-12-02	Sumitomo Chemical Co	2(1H)-Quinozalinones and process therefor
US3642791A (en) *	1969-08-13	1972-02-15	Sandoz Ag	Morpholino-1-substituted-2(1h)-quinazolinones
US4208343A (en) *	1970-10-30	1980-06-17	Westinghouse Electric Corp.	2,4 Diamino benzonitrile
BE785937A (fr) *	1971-07-08	1973-01-08	Sandoz Sa	Nouveaux derives de la quinazoline, leur preparation et leur application comme medicaments
US3937705A (en) *	1972-03-09	1976-02-10	Sandoz, Inc.	1-isopropyl-7-methyl-4-(p-fluorophenyl)-2(1h)-quinazolinone
US4064246A (en) *	1976-10-12	1977-12-20	Sandoz, Inc.	Hydroxymethyl-substituted-2(1H)-quinazolinones
US4071516A (en) *	1976-08-20	1978-01-31	Sandoz, Inc.	4-(Acyloxyphenyl)-quinazolin-2(1H)-ones
US4160092A (en) *	1977-06-16	1979-07-03	E. I. Du Pont De Nemours And Company	Quinazolinone oxides and their use as intermediates for pharmaceutical agents
US4224328A (en) *	1979-04-11	1980-09-23	Sandoz, Inc.	Methods with 1-substituted-4-aryl-quinazolin-2(1H)-ones and thiones and pyrido[2,3-d]pyrimidin-2-ones as platelet aggregation inhibitors
CH645362A5 (de) *	1979-07-05	1984-09-28	Sandoz Ag	Verfahren zur herstellung von 4-phenyl-2(1h)-chinazolinonen.
FR2676042B1 (fr) *	1991-05-02	1993-07-23	Commissariat Energie Atomique	Procede de preparation d'un borohydrure de metal alcalin tel que le borohydrure de lithium.
US6545004B1 (en)	1999-10-27	2003-04-08	Cytokinetics, Inc.	Methods and compositions utilizing quinazolinones
US7230000B1 (en)	1999-10-27	2007-06-12	Cytokinetics, Incorporated	Methods and compositions utilizing quinazolinones
AR038658A1 (es)	2001-06-15	2005-01-26	Novartis Ag	Derivados de 4-aril-2(1h) quinazolinona y 4-aril-quinazolina 2-sustituidas, un proceso para su preparacion, composiciones farmaceuticas y el uso de dichos derivados para la preparacion de un medicamento
US6753428B2 (en) *	2001-11-20	2004-06-22	Cytokinetics, Inc.	Process for the racemization of chiral quinazolinones
WO2003070701A2 (fr) *	2002-02-15	2003-08-28	Cytokinetics, Inc.	Syntheses de quinazolinones
AU2003270015A1 (en)	2002-05-09	2003-12-02	Cytokinetics, Inc.	Compounds, compositions, and methods
WO2003094839A2 (fr) *	2002-05-09	2003-11-20	Cytokinetics, Inc.	Composes, compositions et procedes
JP2005536475A (ja) *	2002-05-23	2005-12-02	サイトキネティクス・インコーポレーテッド	化合物、組成物、および方法
EP1556357A4 (fr) *	2002-06-14	2006-09-13	Cytokinetics Inc	Composes, compositions et procedes
EP1537089A4 (fr) *	2002-07-23	2008-04-16	Cytokinetics Inc	Composes, compositions et procedes
AU2003262747A1 (en) *	2002-08-21	2004-03-11	Cytokinetics, Inc.	Compounds, compositions, and methods
EP1558083A4 (fr) *	2002-09-30	2008-04-16	Cytokinetics Inc	Composes, compositions, et procedes
GB0230015D0 (en) *	2002-12-23	2003-01-29	Novartis Ag	Organic compounds
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1968
- 1968-11-12 BG BG015055A patent/BG16042A3/bg unknown
- 1968-11-12 US US00775201A patent/US3723432A/en not_active Expired - Lifetime
1969
- 1969-10-31 GB GB53620/69A patent/GB1282612A/en not_active Expired
- 1969-10-31 CH CH1624569A patent/CH521972A/de not_active IP Right Cessation
- 1969-11-03 NL NL6916514A patent/NL6916514A/xx not_active Application Discontinuation
- 1969-11-07 FR FR696938404A patent/FR2024830B1/fr not_active Expired
- 1969-11-10 BG BG014693A patent/BG16037A3/bg unknown
- 1969-11-10 OA OA53783A patent/OA03829A/fr unknown
- 1969-11-10 AT AT993271A patent/AT319950B/de not_active IP Right Cessation
- 1969-11-10 BG BG014694A patent/BG16038A3/bg unknown
- 1969-11-10 BG BG013325A patent/BG16188A3/bg unknown
- 1969-11-10 BG BG015469A patent/BG16043A3/bg unknown
- 1969-11-10 BG BG014695A patent/BG16039A3/bg unknown
- 1969-11-10 BG BG014696A patent/BG16040A3/bg unknown
- 1969-11-10 ES ES373377A patent/ES373377A1/es not_active Expired
- 1969-11-10 AT AT1053269A patent/AT310169B/de not_active IP Right Cessation
- 1969-11-10 NO NO4445/69A patent/NO124032B/no unknown
- 1969-11-10 IE IE1526/69A patent/IE33933B1/xx unknown
- 1969-11-10 BE BE741529A patent/BE741529A/xx unknown
- 1969-11-10 BG BG014692A patent/BG16036A3/bg unknown
- 1969-11-10 AT AT993071A patent/AT319949B/de not_active IP Right Cessation
- 1969-11-10 DE DE1956384A patent/DE1956384C3/de not_active Expired
- 1969-11-10 AT AT993571A patent/AT310176B/de not_active IP Right Cessation
- 1969-11-11 SE SE6915448A patent/SE374920B/xx unknown
- 1969-11-11 BR BR214095/69A patent/BR6914095D0/pt unknown
- 1969-11-11 DK DK597169AA patent/DK129347B/da unknown
- 1969-11-11 IL IL33348A patent/IL33348A/xx unknown
- 1969-11-11 SE SE7213438A patent/SE376917B/xx unknown
- 1969-11-12 PL PL1969136872A patent/PL72695B1/pl unknown
- 1969-11-12 ZA ZA697910A patent/ZA697910B/xx unknown
1970
- 1970-05-16 BG BG014697A patent/BG16041A3/bg unknown
- 1970-08-13 BG BG015468A patent/BG15573A3/bg unknown
1972
- 1972-12-08 US US313531A patent/US3925548A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
FR2024830A1 (fr)	1970-09-04
DK129347B (da)	1974-09-30
DE1956384B2 (de)	1980-02-07
FR2024830B1 (fr)	1973-07-13
BR6914095D0 (pt)	1973-02-13
IL33348A (en)	1973-04-30
DE1956384A1 (de)	1970-06-11
AT319949B (de)	1975-01-10
BG16188A3 (bg)	1972-07-20
SE376917B (fr)	1975-06-16
AT319950B (de)	1975-01-10
GB1282612A (en)	1972-07-19
ZA697910B (en)	1971-07-28
IE33933L (en)	1970-05-12
BG16042A3 (bg)	1972-05-20
AT310169B (de)	1973-09-25
SE374920B (fr)	1975-03-24
BG16040A3 (bg)	1972-05-20
BE741529A (fr)	1970-05-11
DE1956384C3 (de)	1980-10-09
USB313531I5 (fr)	1975-01-28
BG16037A3 (bg)	1972-05-20
BG16043A3 (bg)	1972-05-20
AT310176B (de)	1973-09-25
BG16038A3 (bg)	1972-05-20
SU366612A3 (fr)	1973-01-16
BG16036A3 (bg)	1972-05-20
DK129347C (fr)	1975-02-17
US3925548A (en)	1975-12-09
BG16039A3 (bg)	1972-05-20
BG16041A3 (bg)	1972-05-20
US3723432A (en)	1973-03-27
ES373377A1 (es)	1972-05-16
CH521972A (de)	1972-04-30
IE33933B1 (en)	1974-12-11
NL6916514A (fr)	1970-05-14
BG15573A3 (bg)	1976-06-26
NO124032B (fr)	1972-02-21
OA03829A (fr)	1971-12-24
IL33348A0 (en)	1970-01-29

Publication	Publication Date	Title
PL72695B1 (en)	1974-08-30	1-substituted-4-aryl-2(1h)-quinazolinones and their preparation [us3723432a]
KR890001546B1 (ko)	1989-05-08	피라졸 술폰아미드 유도체의 제조방법
HU229515B1 (en)	2014-01-28	Substituted sulfonyl aminomethyl benzoic acid (derivatives) and method for the production thereof
KR970065522A (ko)	1997-10-13	플루오로알킬- 및 플루오로알콕시-치환된 헤테로사이클릭 브라디키닌 길항제, 이의 제조방법 및 이의 용도
AU2001267442B2 (en)	2004-07-01	Process for the preparation of aniline compounds
US4709092A (en)	1987-11-24	Process for the preparation of 2-alkoxybenzosulfonamides
JPH107665A (ja)	1998-01-13	２−（２′−ヒドロキシフェニル）−２ｈ−ベンゾトリアゾール誘導体の調製方法
KR900006837B1 (ko)	1990-09-22	피리미딘 유도체의 제조방법
EP0902019A1 (fr)	1999-03-17	Procedes de preparation d'un compose pyrimidine
US4647677A (en)	1987-03-03	Process for preparing 2,3-dihydro-7-aminobenzofurans
CA2175420C (fr)	2007-04-10	Methode de preparation de derives de substitution facultative en 2 de 5-chloro-imidazole-4-carbaldehydes
GB2053200A (en)	1981-02-04	Thiadiazole carbohydroxamic acid derivatives and their use in a process for the manufacture of 5-mercapto-1,2,3-triazoles
WO1996022284A1 (fr)	1996-07-25	Procede de production de sulfonylurees
Vorob’ev et al.	2007	Intramolecular cyclization of O-(3, 5-dinitrophenyl) and O-(3-amino-5-nitrophenyl) ketoximes, products of transformations of 1, 3, 5-trinitrobenzene. The synthesis of nitrobenzo [b] furans and 4-hydroxynitroindoles
US4599428A (en)	1986-07-08	Process for the preparation of 5(6)-thio substituted benzimidazoles
US4259502A (en)	1981-03-31	Process for the preparation of 5-mercapto-1,2,3-triazoles
AU686761B2 (en)	1998-02-12	Process for preparing (1H-tetrazol-5-yl)tetrazolo (1,5-a) quinolines and naphthyridines
JP4138067B2 (ja)	2008-08-20	メチン誘導体の製造方法
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SU1669913A1 (ru)	1991-08-15	Способ получени 5-или 6-замещенных 9-бромбензимидазо [2,1-в] хиназолинонов-12(6 или 5Н)
SU472503A3 (ru)	1975-05-30	Способ получени производных 3аминопиразолона-5
KR940011436A (ko)	1994-06-21	플루오로알킬(렌) 그룹을 함유하는 o-페닐렌디아민
JP2865715B2 (ja)	1999-03-08	親電子芳香族化合物のヒドロキシル化方法
US5567825A (en)	1996-10-22	Method for the preparation of a triazole compound